The author is a Forbes contributor. The opinions expressed are those of the writer.

Loading ...

Loading ...

This story appears in the {{article.article.magazine.pretty_date}} issue of {{article.article.magazine.pubName}}. Subscribe

This is a guest post by Kaycee Krysty, president emerita of Laird Norton Tyee, a Seattle‐based wealth management firm. Kaycee spearheads the firm’s ReGenU effort focused on helping clients plan for life’s transitions. She is working on a book and speaks and blogs about life’s transitions and investing in human capital.

Kaycee Krysty and her husband have heart-to-heart talks in the car. Their dog Sergeant Pepper also loves a good road trip.

Over the holidays I happened to be in a store that featured traditional toys. Among the wooden trains and the model airplane sets, there it was Highway Bingo! What a blast from the past.

If you are a baby boomer like me, you may remember this game. It looks like regular bingo cards but the little spaces have things you might see along the side of the road, like a tractor, a windmill or a gas pump. My sister and I were wildly competitive in the big backseat of my mom's 1943 Plymouth sedan, seeing who could discover these things most quickly. Unconstrained by seatbelts (historical footnote: cars didn’t have them in those days), we’d press our faces against the side windows trying to spot an elusive scarecrow.

As an adult, a road trip is an opportunity for another kind of discovery. We boomers are facing many of life's transitions – looming retirement, loss of parents, physical changes, to name a few. So now, more than ever, we need to be defining and pursuing the things that matter most to us. Yet the pace of our busy lives rarely offers time to think about these things let alone talk about them. A road trip can offer the perfect setting for the kinds of thoughtful conversations we need to have in a changing world.

Many couples, like my husband Michael and I, find that some of their best conversations take place in the car. Maybe it is being locked together in a moving box. Or could it be the thrill of the open road?

Often times, car rides give us that rare opportunity to spend time alone together. (Actually, Michael and I are seldom truly alone; there is always a dog in the car.) In the car you seem to be able to have the space to go deep on the issues. And that's what's we need to consider the big issues in life.

Over the years I've compiled a list of questions that I offer clients and friends as fodder for these road trip heart-to-hearts. Here are five that many people have told me get some particularly juicy conversations going:

1. What do you care enough about that you would argue with someone over it at a very nice dinner party?

2. What is a perfect day like? Can you provide vivid details?

3. How do others know what matters to you? Can you name the ways you walk your talk?

4. Let's say you have been dead for 10 years. Are you still making a difference in people's lives? How? Or do you even care?

5. Describe what success looks like for your children (if you are parents). What do you want most for them?

These five questions can keep you going for a thousand miles. There is so much to discover, even for those of us who have been taking road trips together for many years. So schedule a trip soon. Not only could you learn something new about each other but you may find new direction for the road ahead, more confident that you are clearly pointed at what matters most. And that's what I call a bingo.

What topics have you covered in road trip heart-to-hearts? Please tell us in the comment space below.